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Will Fritz and Casey Baum have spent years perfecting the sidekick schtick. They grew up doing children’s theater in Annapolis, where they’ve played buddies in stage productions of everything from the Addams Family to Twelfth Night. So when they take the stage at Maryland Hall to pitch their short documentary they are calling “The Lookout,” they are confident in their repartee.

But even though they’ve moved far away to pursue film careers, the story they’re pitching hits close to home. “The Lookout” will examine the way the media covered the arrest and trial of their Annapolis Key School social studies teacher, Diana Toebbe, for selling Navy secrets to a foreign government.

“This is a film about us as filmmakers understanding our own responsibility as filmmakers,” said Fritz from his home in Savannah, Georgia. “We will use Diana’s story as a lens to examine the weird cultural landscape we live in and how characters can be changed… We don’t want to defend what she did, but maybe cut back the hate and make it more about understanding why she did what she did and how she got in that position. Here is someone who is a doctor, a mother, a teacher who taught us all we know about US history…and she was arrested by the US government.”

Fritz and Baum are veterans of the Annapolis Film Fest, having participated in Patti White and Lee Anderson’s Filmster’s Academy for years before graduating from Key School in 2018 and heading off to the Savannah College of Art and Design and Temple University, respectively.

On the Key School campus, Toebbe was “a caretaker,” the teacher who wrote their college recommendations, the teacher whose classroom students could retreat to “when they were upset with the world,” recalled Baum, who lives in Los Angeles. 

For Fritz and Baum, both 23, memories of their favorite teacher are freighted now with images of her in an orange jumpsuit, as she was depicted in drawings from her 2022 trial. Her former students were transfixed and horrified, watching the news tell the story of someone they barely recognized.

“We know we watched the news and the ruling judge in his final statement, said, ‘This is a story out of the movies.’” Fritz recalled. “And Casey and I knew then that it was an idea that would be shared. And we didn’t want it done by someone who didn’t know her as well as we did.

They hope to be the first media to be able to interview Toebbe and get her perspective. Baum said that telling such stories with empathy is part of their vision for a “better tomorrow.”

“I’m really hopeful that our intention to do this with as much empathy and creativity as possible will shed light on the topic and how it was interpreted by the media,” Baum said.